title: Identification, isolation and characterization of impurities of clindamycin palmitate hydrochloride.
abstract: Clindamycin palmitate hydrochloride is a water soluble hydrochloride salt of the ester of clindamycin and palmitic acid. It is inactive in vitro, rapid in vivo hydrolysis converts this compound to the antibacterially active clindamycin. Total 12 impurities at levels ranging from 0.05% to 0.5% were detected by isocratic reverse-phase high performance liquid chromatography (HPLC) using RI detector. The molecular weights of impurities were determined by LC-MS analysis. Two impurities were starting materials and the remaining impurities were isolated from crude samples/enriched mother liquors using reverse-phase preparative HPLC. Based on the spectral data the structures of these impurities were characterized as, clindamycin palmitate sulphoxides alpha-/beta-isomers (impurity I); clindamycin laurate (impurity II); lincomycin palmitate (impurity III); clindamycin myristate (impurity IV); epiclindamycin palmitate (impurity V); clindamycin palmitate 3-isomer (impurity VI); clindamycin pentadecanoate (impurity VII); clindamycin B-palmitate (impurity VIII); clindamycin heptadecanoate (impurity IX) and clindamycin stearate (impurity X). Structural elucidation of all impurities by spectral data ((1)H NMR, (13)C NMR, MS and IR) and formation of these impurities have been discussed in detail.
authors.affiliation: A.P.L. Research Centre, 313 Bachupally, Hyderabad 500072, India.
authors.forename: Ch
authors.initials: Ch
authors.lastname: Bharathi
authors.forename: P
authors.initials: P
authors.lastname: Jayaram
authors.forename: Joseph
authors.initials: J
authors.lastname: Sunder Raj
authors.forename: M
authors.initials: M
authors.lastname: Saravana Kumar
authors.forename: V
authors.initials: V
authors.lastname: Bhargavi
authors.forename: V K
authors.initials: VK
authors.lastname: Handa
authors.forename: Ramesh
authors.initials: R
authors.lastname: Dandala
authors.forename: A
authors.initials: A
authors.lastname: Naidu
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002981:Clindamycin / Q000031:analogs & derivatives* / Q000737:chemistry; D004340:Drug Contamination; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D008970:Molecular Weight; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000900:Anti-Bacterial Agents; D002981:Clindamycin; C000489:clindamycin palmitate